3-[2-(4-Chlorophenoxy)phenyl]-4-hydroxy-1-methylpyrrolidine-2-one → cis-5-chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz-[2,3:6,7]oxepino[4,5-c]pyrrol-1-one

HRID 2040933

Reaction equation

[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH:13]2[CH:17](O)[CH2:16][N:15]([CH3:19])[C:14]2=[O:20])=[CH:4][CH:3]=1>ClCCl>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[O:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C@@H:13]3[C:14](=[O:20])[N:15]([CH3:19])[CH2:16][C@@H:17]3[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 3 g (9.4 mmol) of 3-[2-(4-chlorophenoxy)phenyl]-4-hydroxy-1-methylpyrrolidine-2-one (compound XIIIb) and 40 g of polyphosphoric acid was stirred overnight at 110° C. After cooling down to room temperature, the resulting mixture was poured into 150 mL of an ice-water mixture. 100 mL of dichloromethane were added, and the organic phase was extracted. The aqueous phase was washed with 50 mL of dichloromethane. The organic phases were combined, washed with brine, and evaporated under vacuum. The crude product was purified by column chromatography to obtain 0.5 g of cis-5-chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz[2,3:6,7]oxepino[4,5-c]pyrrol-1-one (compound cis-VIb). Yield: 17.7%.

Workup

temperatureAfter cooling down to room temperature
extractionthe organic phase was extracted
washThe aqueous phase was washed with 50 mL of dichloromethane
washwashed with brine
customevaporated under vacuum
customThe crude product was purified by column chromatography

Sources & evidence

ORD record: ord-3a05f1c2840f4af4a9c91fc97f2207ac
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580972B2

Linked notes

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